WO2007125952A1 - Ｎｐｙ ｙ５受容体拮抗作用を有するアミン誘導体 - Google Patents

Ｎｐｙ ｙ５受容体拮抗作用を有するアミン誘導体 Download PDF

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Publication number
WO2007125952A1
WO2007125952A1 PCT/JP2007/058938 JP2007058938W WO2007125952A1 WO 2007125952 A1 WO2007125952 A1 WO 2007125952A1 JP 2007058938 W JP2007058938 W JP 2007058938W WO 2007125952 A1 WO2007125952 A1 WO 2007125952A1
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WIPO (PCT)
Prior art keywords
substituent
chemical
compound
lower alkyl
optionally substituted
Prior art date
Application number
PCT/JP2007/058938
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English (en)
French (fr)
Japanese (ja)
Inventor
Takayuki Okuno
Naoki Kouyama
Masahiro Sakagami
Original Assignee
Shionogi & Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Priority to CN200780024349.7A priority Critical patent/CN101479238B/zh
Application filed by Shionogi & Co., Ltd. filed Critical Shionogi & Co., Ltd.
Priority to MX2008013511A priority patent/MX2008013511A/es
Priority to AU2007244358A priority patent/AU2007244358B2/en
Priority to EP07742373.9A priority patent/EP2017261A4/en
Priority to CA002650683A priority patent/CA2650683A1/en
Priority to US12/226,516 priority patent/US9150507B2/en
Priority to NZ572381A priority patent/NZ572381A/en
Priority to KR1020087026246A priority patent/KR101441146B1/ko
Priority to BRPI0710950-4A priority patent/BRPI0710950A2/pt
Priority to JP2008513237A priority patent/JP4528901B2/ja
Publication of WO2007125952A1 publication Critical patent/WO2007125952A1/ja
Priority to NO20084983A priority patent/NO20084983L/no
Priority to US12/823,568 priority patent/US9139518B2/en

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    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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    • C07C311/05—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
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    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C—CHEMISTRY; METALLURGY
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    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Definitions

  • the present invention relates to a novel compound having an NPY Y5 receptor antagonistic activity and useful as a pharmaceutical, particularly as an anti-obesity drug.
  • NPY neuropeptide
  • NPY has been found to have feeding, anticonvulsant, learning promoting, anti-anxiety, anti-stress, etc. in the central nervous system.
  • central nervous system diseases such as depression, Aruno, ima type 1 dementia, and Parkinson's disease.
  • NPY causes contraction of smooth muscles such as blood vessels and myocardium, and is thought to be involved in cardiovascular disorders.
  • metabolic diseases such as obesity, diabetes, and hormonal abnormalities (see Non-Patent Document 1). Therefore, an NPY receptor antagonist may be a preventive or therapeutic agent for various diseases involving the NPY receptor as described above.
  • Patent Document 1 Amine derivatives having a sulfonyl group having a structure similar to that of the compound according to the present invention and having an NPY-5 receptor antagonistic activity are described in Patent Document 1, Patent Document 2, Patent Document 3, Patent Document 4, and the like. ing.
  • Patent Literature 5, Patent Literature 8, Patent Literature 9, Patent Literature 10, and Patent Literature 11 describe that amide derivatives having a sulfonyl group have NPY-5 antagonistic activity.
  • Patent Document 12 also describes a derivative having a sulfonyl group having an NPY ⁇ 5 receptor antagonistic action. These compounds differ in structure from the compounds of the present invention.
  • Patent Document 6 compounds having a similar structure to the compound according to the present invention are described in Patent Document 6, Patent Document 7, Patent Document 13, Patent Document 14, and the like. It is not something that suggests.
  • Non-patent literature l Trends in Pharmacological Sciences, Vol. 15, 153 (1994)
  • Non-Patent Document 2 Trends in Pharmacological Sciences, Vol.18, 372 (1997)
  • Non-Patent Document 3 Peptides, Vol.18, 445 (1997)
  • Patent Document 1 International Publication No. 01Z002379 Pamphlet
  • Patent Document 2 Pamphlet of International Publication No. 00Z064880
  • Patent Document 3 International Publication No. 99Z055667 Pamphlet
  • Patent Document 4 Pamphlet of International Publication No. 00Z068107
  • Patent Document 5 International Publication No. 01Z037826 Pamphlet
  • Patent Document 6 International Publication No. 2006Z014482 Pamphlet
  • Patent Document 7 International Publication No. 2005Z097738 Pamphlet
  • Patent Document 8 International Publication No. 97Z20823 Pamphlet
  • Patent Document 9 US Patent Application Publication No. 2006Z293341 Pamphlet
  • Patent Document 10 International Publication No. 2007Z002126 Pamphlet
  • Patent Document 11 Pamphlet of International Publication No. 2006Z001318
  • Patent Document 12 International Publication No. 2005Z080348 Pamphlet
  • Patent Document 13 US Patent Application Publication No. 2007Z060598 Pamphlet
  • Patent Document 14 International Publication No. 2005Z121107 Pamphlet
  • An object of the present invention is to provide a novel compound having an excellent NPY Y5 receptor antagonistic action.
  • An object of the present invention is to provide a novel compound having an excellent NPY Y5 receptor antagonistic action.
  • R 1 has a substituent, and may be lower alkyl
  • Y is —S (0) n— (where n is 1 or 2) or —CO—
  • R 2 has hydrogen or a substituent, and may be lower alkyl
  • R 1 and R 2 together may form a lower alkylene
  • R 7 has hydrogen or a substituent, and may be lower alkyl
  • Having a substituent may be lower alkylene
  • R 3 , R 4 , R 5 and R 6 are each independently hydrogen or a lower alkyl optionally having substituent (s);
  • May have a substituent may have a cycloalkylene, have a substituent! /, May have a cycloalkylene, an optionally substituted bicycloalkylene, have a substituent
  • An arylene or an optionally substituted heterocycle, p and q are each independently an integer of 0 to 2, and one of p and q is not 0,
  • R 14 has a substituent and may be a phenol]! /,
  • Z may have a substituent, may be lower alkyl, may have a substituent! /, May have a lower alkyl
  • -Amino, optionally substituted amino, lower alkoxy optionally substituted may have a substituent, hydrocarbon cyclic group, have a substituent ⁇ is a heterocyclic group,
  • Z is a three-ring condensed heterocyclic group, an optionally substituted thiazolyl or a substituent, but not quinazolinyl! /,)]
  • R 1 is an optionally substituted alkyl having 2 to 10 carbon atoms, the compound according to (1), a pharmaceutically acceptable salt thereof, or a solvate thereof,
  • Z is an optionally substituted heterocyclic group, the compound according to (5), a pharmaceutically acceptable salt thereof, or a solvate thereof,
  • May have a substituent may be cycloalkylene, have a substituent! /, May have a cycloalkylene, have a substituent, may be a bicycloalkylene or a substituent.
  • May have a substituent may be cyclohexylene or may have a substituent, and may be piperidinylene,
  • p and q are each independently 0 or 1, and one of p and q is not 0, (5) the compound according to (5), a pharmaceutically acceptable salt thereof, or a solvate thereof,
  • Z has a substituent! /, May! /, Lower alkyl, has a substituent! /, Or may have a phenyl or optionally substituted pyridyl , Optionally substituted pyrazolyl, optionally substituted isoxazolyl, optionally substituted oxadiazolyl, optionally substituted pyridazil, substituted A pyrazinyl optionally having a substituent! /, Or a pyrimidyl or a substituent, which may be a condensed heterocyclic ring of two rings, (7) Or the compound according to (8), a pharmaceutically acceptable salt thereof or a solvent thereof,
  • R 1 has a substituent! /, May! /, Lower alkyl
  • R 2 has hydrogen or a substituent, and may be lower alkyl
  • R 7 has hydrogen or a substituent, and may be lower alkyl
  • R 5 and R 6 are each independently hydrogen
  • Z may have a substituent, or may have a hydrocarbon cyclic group or a substituent! / ⁇ Heterocyclic group] Or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable salt thereof (provided that Z is a tricyclic fused heterocyclic group or a substituent, and may be pyrimidyl) Solvates,
  • Z has a substituent! /, May! /, A phenol, has a substituent! /, May be indanyl, an optionally substituted pyridyl, Pyridazil optionally having a substituent, Pyrimidyl optionally having a substituent, Pyrazolyl optionally having a substituent, Having a substituent !, or Isoxazolyl , Having a substituent! /, Oxazodialyl, or optionally having two substituents, a compound of (12), or a pharmaceutically acceptable salt thereof Or solvates thereof,
  • Z may have a substituent, may be isoquinolyl, have a substituent! /, May be benzothiazolyl, optionally have benzoxazolyl, have a substituent Benzopyridyl, optionally substituted benzopyridyl, optionally substituted benzoimidazolyl, optionally substituted thiazolopyridyl, substituted Isoxazolinol which may have, oxazolinol which may have a substituent, benzoxazinol or a substituent, which may have a benzoxazinol or a substituent.
  • R 1 has a substituent, and may be lower alkyl
  • Y is S (O) —
  • R 2 has hydrogen or a substituent, and may be lower alkyl
  • R 7 has hydrogen or a substituent, and may be lower alkyl
  • R is substituted and may be a phenol
  • Z may have a substituent, or may have a hydrocarbon cyclic group or a substituent! / ⁇ Heterocyclic group]
  • Z may have a substituent, an optionally substituted phenyl, an optionally substituted pyridyl, an optionally substituted pyridazil, and optionally substituted.
  • R 1 has a substituent! /, May! /, Lower alkyl
  • R 2 has hydrogen or a substituent, and may be lower alkyl
  • R 7 has hydrogen or a substituent, and may be lower alkyl
  • R 3 and R 4 are each independently hydrogen
  • Z is a phenyl group optionally having substituents, pyridyl optionally having substituents, pyridazyl optionally having substituents, pyrazinyl optionally having substituents, Pyrimidyl which may have a substituent, quinolyl which may have a substituent, isoquinolyl which may have a substituent, benzothiazolyl which may have a substituent, Benzoimidazolyl which may have, Benzoxazolyl which may have a substituent, Thiazolopyridyl or which may have a substituent, or Oxazolopyridyl which may have a substituent Or a pharmaceutically acceptable salt thereof or a solvate thereof, (18) a compound according to any one of (1) to (17), a pharmaceutically acceptable salt thereof or the Pharmaceutical compositions containing these solvates as active ingredients,
  • An NPY Y5 receptor antagonist comprising the compound according to any one of (1) to (17), a pharmaceutically acceptable salt thereof or a solvate thereof as an active ingredient,
  • R 1 is ethyl or tert-butyl, a salt thereof or a solvate thereof
  • R 1 is ethyl, isopropyl or tert-butyl, a salt thereof or a solvate thereof,
  • Z is a hydrocarbon cyclic group which may have a substituent or a heterocyclic group which may have a substituent, a salt thereof or a solvate thereof.
  • z is an optionally substituted pyridyl, an optionally substituted pyridazil, an optionally substituted pyridyl, an optionally substituted pyrimidinyl, a substituted Quinolyl optionally having a substituent, isoquinolyl optionally having a substituent, benzothiazolyl optionally having a substituent, benzoxazolyl optionally having a substituent, having a substituent Benzopyridyl, which may have a substituent, Benzopyridyl, which may have a substituent, Benzimidazolyl, which has a substituent, Benzimidazolyl, which has a substituent!
  • Benzoxazolyl It may have a substituent, may have a thiazolopyridyl substituent, may have an isoxazolinol, may have a substituent, may have an oxazolinonyl, may have a substituent Benzoxazinol or substituent Or a benzoxazepinol), a salt thereof or a solvate thereof.
  • the compound of the present invention exhibits NPY Y5 receptor antagonism, and the compound of the present invention is a pharmaceutical, particularly an eating disorder, obesity, anorexia nervosa, sexual disorder, reproductive disorder, depression, epileptic seizure
  • Halogen includes fluorine, chlorine, bromine and iodine. Particularly preferred are fluorine and chlorine.
  • Protecting groups for "protected and hydroxy" and “protected! And hydroxy lower alkyl” include all conventionally used hydroxy protecting groups.
  • acyl acetyl, trichloroacetyl, benzoyl, etc.
  • lower alkoxy carbo yl t-butoxy carb, etc.
  • lower alkyl sulphone methane sulphone etc.
  • lower alkoxy lower alkyl methoxymethyl etc.
  • Trialkylsilyl t-butyldimethylsilyl, etc.
  • “Lower alkyl” includes straight-chain or branched alkyl having 1 to L0, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, Examples thereof include tert-butynole, n-pentyl, isopentyl, neopentyl, hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n nonyl and n decyl.
  • “Lower alkyl” in R 1 is preferably 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms, and most preferably ethyl, isopropyl or t-butyl.
  • “Lower alkyl” in other cases preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms.
  • Examples of the substituent of “lower alkyl which may have a substituent” in Z include, for example, (1) halogen; (2) cyan;
  • Substituent group as defined below, ⁇ force optionally substituted with one or more substitutable groups selected (0 hydroxy, GO lower alkoxy, (iii) mercapto, Gv) lower alkyl thio, (V) acyl, (vi) acyloxy, (vii) carboxy, (viii) lower alkoxy carbo
  • Equation (4)
  • R and R are each independently hydrogen or lower alkyl, and when two or more R and Z or R 11 are present, each R 1C> and R 11 may be different.
  • W is a single bond, 0, S or NR 12 ,
  • R 12 is hydrogen, lower alkyl or phenol
  • Each is a cycloalkyl group, bicycloalkyl group, cycloalkenyl group, aryl group or heterocyclic group optionally substituted with one or more substitutable groups selected from the substituent group a defined below.
  • s is an integer from 0 to 4)
  • the substituent group a is (1) halogen; (2) oxo; (3) cyan; (4) -toro; (5) substituted with lower alkyl or hydroxy. Imino;
  • Substituent group ⁇ lower alkyl, lower alkoxy lower alkyl, optionally protected hydroxy lower alkyl, halogeno lower alkyl, lower alkyl sulfol and / or aryl sulfol, respectively.
  • Substituent group ⁇ , lower alkyl, halogeno lower alkyl and / or oxo may be substituted (0 phenol, (ii) naphthyl, (iii) phenoxy, (iv) phenol) Lower alkoxy, (V) phenolthio, (vi) phenol lower alkylthio, (vii) phenolazo, (viii) heterocyclic group, (ix) heterocyclicoxy, (X) heterocyclicthio, (xi And (xii) a heterocyclic sulfonyl.
  • Preferred examples of the substituent group a as a substituent in the ring B are halogen; nitro; hydroxy, optionally substituted lower alkyl (wherein the substituents are halogen, cyan, phenyl) , Carboxy and z or lower alkoxycarbo));
  • Lower alkoxy which may have a substituent (wherein the substituent is halogen, hydroxy, lower alkoxy, carboxy, lower alkoxycarbole, lower alkylamino and z or cyan);
  • It may have a substituent, and may be a heterocyclic group (wherein the substituent may be protected, hydroxy; mercapto; halogen; lower alkyl; cycloalkyl; lower alkoxycarbol; amino). Lower alkoxy carboamino; force rubamoyl; oxo; phenol; lower alkyloxyphenyl; or heterocyclic group), more preferably halogen; substituted with halogen; lower alkyl; Substituted with a halogen is a lower alkoxy.
  • Substituent group ⁇ may be halogen, protected, hydroxy, mercapto, lower alkoxy, lower alkenyl, amino, lower alkylamino-substituted lower alkoxy carbolumino, lower alkylthio, acyl, carboxy, It is a group consisting of lower alkoxy carb, strong rubermoyl, cycloalkyl, cycloalkyl, phenol, phenoxy, lower alkyl phenol, lower alkoxide, halogen phenol, naphthyl and heterocyclic basic groups.
  • Substituents of "lower alkyl which may have a substituent" other than include one or more groups selected from the substituent group ⁇ force. Any position can be substituted with these substituents! /.
  • Examples of the substituent of "having a substituent and may be lower alkoxy" include one or more groups in which the substituent group ⁇ force is also selected, preferably a phenyl or lower alkylphenyl. , Lower alkoxyphenyl, naphthyl or heterocyclic group.
  • Cycloalkyl includes cyclic alkyl having 3 to 8 carbon atoms, preferably 5 or 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • substituents of “having a substituent and may be cycloalkyl” include one or more groups in which substituent group a force is also selected, and any position is substituted.
  • Bicycloalkyl includes a group in which two rings share two or more atoms and an aliphatic ring force of 5 to 8 carbon atoms also removes one hydrogen. Specific examples include bicyclic [2.1.0] pentyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl and bicyclo [3.2.1] octyl. .
  • the "lower alcohol” is a straight chain having 2 to 10 carbon atoms, preferably 2 to 8 carbon atoms, more preferably 3 to 6 carbon atoms, having one or more double bonds at any position. Includes branched alkenyl. Specifically, bur, probe, isoprobe, butur, isobuteninore, preninore, butageninore, penteninore, isopenteninore, pentageninore, hexenore, isohexenyl, hexagenyl, heptenyl, octenyl , Nonenyl, decenyl and the like.
  • Substituents of "having a substituent! /, May! /, Lower alkyl” include halogen, lower alkoxy, lower alcohol, amino-containing lower alkylamino-containing lower alkoxycarbo Le Examples include amino-substituted lower alkylthio, acyl, carboxy, lower alkoxycarbonyl, strong rubamoyl, cycloalkyl-containing cycloalkyl, phenyl, lower alkylphenyl, lower alkoxyphenyl, naphthyl and z or heterocyclic group.
  • Acyl is (1) a linear or branched alkyl or alkyl carbonate having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and most preferably 1 to 4 carbon atoms. And (2) cycloalkyl carbonyl having 4 to 9 carbon atoms, preferably 4 to 7 carbon atoms, and (3) 7 to C: aryl reels having L 1.
  • Cycloalkenyl includes those having one or more double bonds at any position in the ring of the cycloalkyl, specifically cyclocyclopropyl, cyclobuthl, cycla. Examples thereof include oral pen tail, cyclohexane and cyclohexagel.
  • Examples of the substituent of "having a substituent, which may be cycloalkenyl” include one or more groups in which the substituent group ⁇ force is also selected.
  • substituent of "having a substituent may be an amino"
  • the substituent group ⁇ the substituent having V, the benzoyl and / or the substituent having ! /, May! /
  • Heterocyclic carbocycles wherein the substituents are hydroxy, lower alkyl, lower alkoxy and ⁇ or lower alkylthio).
  • aryl is a monocyclic or polycyclic aromatic carbocyclic group, and includes phenyl, naphthyl, anthryl, phenanthryl and the like. Further, aryls condensed with other non-aromatic hydrocarbon cyclic groups are also included, and specific examples include indanyl, indul, bifuryl, acenaphthyl, tetrahydronaphthyl and fluorenyl. In particular, ferrule is preferable.
  • “Having a substituent, may be aryl” and “having a substituent, may be! / ⁇ phenyl” in ⁇ are the substituent group a, the substituent group a force, the selectable substituent Place with one or more groups Substituted with! /, May! /, Lower alkyl, etc. may include “aryl” and “far”.
  • Substituents other than Z may have a substituent, may be aryl, and may have a substituent may be! /, Phenyl. 1 or more groups selected from
  • Hydrocarbon cyclic group includes the above “cycloalkyl”, “cycloalkenyl”, “bicycloalkyl” and “aryl”.
  • non-aromatic hydrocarbon cyclic group includes the above “cycloalkyl”, “cycloalkenyl” and “bicycloalkyl”.
  • hydrocarbon cyclic group which may have a substituent is the above-mentioned "having a substituent, may be a V cycloalkyl", “has a substituent, Including “cycloalkenyl”, "V having a substituent, may be bicycloalkyl” and "having a substituent! /, May! /, Aryl"
  • the "heterocyclic group” includes a heterocycle having 0, S, and a repulsive force and one or more optionally selected heteroatoms in the ring, specifically pyrrolyl, imidazolyl, pyrazolyl, 5- to 6-membered heteroaryls such as pyridyl, pyridazyl, pyrimidyl, pyrajyl, triazolyl, triazyl, tetrazolyl, isoxazolyl, oxazolyl, oxadiazolyl, isothiazolyl, thiazolyl, thiadiazolyl, furyl and chenyl; indolyl, isoindoli , Indazolyl, indolizyl, indolyl, isoindoleyl, quinolyl, isoquinolyl, cinnolinyl, phthalajur, quinazolinyl, naphthyridinyl, quinox
  • a condensed heterocyclic group (for example, benzothiazolyl and the like) condensed with a ring other than a heterocyclic ring may have a bond on any ring.
  • Substituents of "having a substituent, may be a heterocyclic group" and “having a substituent, may be a bicyclic fused heterocyclic group” are the above-mentioned “substituted It has the same group as “Areel”.
  • heterocyclic group moiety of “heterocyclic carbocycle”, “heterocyclic oxy”, “heterocyclic thio” and “heterocyclic substituted phenyl” is the same as the above “heterocyclic group”.
  • the "lower alkylene” includes a divalent group in which 1 to 6, preferably 2 to 6, more preferably 3 to 6 methylenes are continuous, specifically methylene, ethylene, Examples include trimethylene, tetramethylene, pentamethylene and hexamethylene. Particularly preferred is tetramethylene.
  • lower alkylene part of “lower alkylenedioxy” is the same as the above “lower alkylene”, and is preferably methylenedioxy or ethylenedioxy.
  • “Lower alkylene” is a divalent group in which 2 to 6, preferably 3 to 6, more preferably 4 to 5 methylenes are continuous, and has at least one carbon-carbon bond. In which one is a double bond.
  • Cycloalkylene is a divalent group formed by removing one hydrogen atom from the above “cycloalkyl”.
  • cycloalkylene 1,4-cyclohexanediyl is preferred.
  • the “cycloalkene” includes a group having at least one double bond in the ring of the cycloalkylene.
  • Bicycloalkylene includes a group in which one hydrogen is further removed from the above “bicycloalkyl”. Specific examples include bicyclo [2.1.0] pentylene, bicyclo [2.2.1] heptylene, bicyclo [2.2.2] octylene, bicyclo [3.2.1] octylene.
  • the "heterocyclic diyl” includes a divalent group formed by removing one hydrogen atom from the above “heterocyclic group”.
  • Preferred are piperidine, piperazine, pyridine, pyrimidine, pyrazine, pyrrolidine and pyrrole, more preferably piperidine.
  • “Arylene” includes a divalent group formed by removing one hydrogen atom from the above “aryl”. Preferred is phenylene.
  • heteroarylene includes those having the aromatic attribute among the above “heterocyclic diles”. Specifically, pyrrole dil, imidazole dil, pyrazole dil, pyridine dil, pyridazine dil, pyrimidine dil, pyrazine dil, triazole dil, triazin dil, isoxazole dil, oxazole dil, oxadizol dil, isothiazole And diazyl, thiazol diyl, thiadiazole dill, frangil and thiophene diyl.
  • “Alternative, may be lower alkylene”, “Substituent may be, lower alkyl” ⁇ Kelen '', ⁇ optionally substituted cycloalkylene '', ⁇ optionally substituted V ⁇ cyclohexylene '', ⁇ substituted)! / /, Bicycloalkylene, “optionally substituted cycloalkene”, “optionally substituted phenolene”, “having a substituent!
  • substituents of “ring diyl” and “having a substituent, may be piberidylene” include one or more substitutable groups selected from the substituent group ⁇ force, preferably halogen, hydroxy Lower alkyl, halogeno lower alkyl, lower alkoxy, amino-containing lower alkylamino-containing acyl, carboxy or lower alkoxycarbo yl and the like. Any position can be substituted with these groups!
  • the compound according to the present invention includes a pharmaceutically acceptable salt capable of producing each compound.
  • “Pharmaceutically acceptable salts” include, for example, salts of inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid or phosphoric acid; salts of organic acids such as paratoluenesulfonic acid, methanesulfonic acid, oxalic acid or citrate; Examples include salts of organic bases such as sodium, trimethylammonium and triethylammonium; alkali metal salts such as sodium or potassium; and alkaline earth metal salts such as calcium or magnesium. .
  • the compound according to the present invention includes its solvate and is directed to the compound (I).
  • it is a hydrate, and one molecule of the compound according to the present invention may be coordinated with an arbitrary number of water molecules.
  • the compound (I) according to the present invention has an asymmetric carbon atom, it includes racemates, both enantiomers and all stereoisomers (geometric isomers, epimers, enantiomers, etc.) . In addition, this departure In the case where the compound (I) according to the invention has a double bond, it includes both the E-form and the Z-form.
  • X is cycloalkylene, both cis and trans isomers are included.
  • the compound (I) according to the present invention can be synthesized, for example, by the following method.
  • X is described as CH 2—G or G—CH 2—.
  • solvents include tetrahydrofuran, dimethylformamide, jetyl ether, dichloromethane, toluene, benzene, xylene, cyclohexane, hexane, chloroform, ethyl acetate, butyl acetate, pentane, heptane, dioxane, acetone, acetonitrile. Water and A mixed solvent thereof or the like can be used.
  • the reaction conditions are the same as in step A above.
  • Compound 3 in which n 2 is obtained by subjecting Compound 5 obtained in Step B to an acid reaction by a conventional method.
  • oxidizing agent m-chloroperbenzoic acid, peracetic acid, hydrogen peroxide, pertrifluoromethylacetic acid, sodium periodate, sodium hypochlorite, potassium permanganate, etc. can be used. What is necessary is just to carry out at 0 to 50 degreeC.
  • Solvents include tetrahydrofuran, dimethylformamide, jetyl ether, dichloromethane, toluene, benzene, xylene, cyclohexane, hexane, chloroform, ethyl acetate, butyl acetate, pentane, heptane, dioxane, acetone, acetonitrile, water , Methanol, ethanol, isopropanol, and mixed solvents thereof can be used.
  • Compound 6 obtained in step A or C is treated with a base in an appropriate solvent to obtain compound 6.
  • a base barium hydroxide, sodium hydroxide, potassium hydroxide, hydrazine, propanthiol lithium salt and the like can be used, and as the solvent, tetrahydrofuran, dimethylformamide, dioxane, acetone, acetonitrile, methanol, ethanol, propano And water, and mixed solvents thereof can be used.
  • the reaction may be performed at 0 ° C to 100 ° C for several minutes to several tens of hours.
  • Compound 8 obtained by reacting Compound 6 obtained in Step D with amino compound 7 having substituents Z and R 7 corresponding to the target compound in an appropriate solvent at 0 ° C to 50 ° C for several minutes to several hours.
  • Solvents include tetrahydrofuran, dimethylformamide, jetyl ether, dichloromethane, toluene, benzene, xylene, cyclohexane, hexane, chloroform, ethyl acetate, butyl acetate, pentane, heptane, dioxane, acetone, acetonitrile, water. And a mixed solvent thereof can be used. If necessary, an activator such as salt thiol, acid halide, acid anhydride, or active ester may be used. Process F
  • the obtained compound 8 is treated with a suitable reducing agent in a suitable solvent to obtain compound (IA).
  • a suitable reducing agent sodium borohydride, lithium borohydride, lithium aluminum hydride, etc. can be used.
  • the solvent tetrahydrofuran, dimethylformamide, dioxane, acetonitrile, methanol, ethanol, propanol, acetic acid and the like.
  • a mixed solvent or the like can be used. Just react at 0 ° C ⁇ 100 ° C for several minutes to tens of hours! Process G
  • Compound 6 obtained in Step D is treated with a reducing agent in an appropriate solvent to obtain Compound 9.
  • a reducing agent sodium borohydride, lithium borohydride, lithium aluminum hydride, diborane, etc.
  • the solvent tetrahydrofuran, dimethylformamide, dioxane, acetonitrile, methanol, ethanol, propanol and A mixed solvent thereof can be used.
  • the reaction may be carried out at 0 ° C. to 100 ° C. for several minutes to several tens of hours. If necessary, it may be carried out via an intermediate such as an acid halide, an acid anhydride, or an active ester.
  • Compound 10 is obtained by subjecting compound 9 obtained in step G to acid-acid reaction by a conventional method.
  • oxidizing agents m-chloroperbenzoic acid, peracetic acid, hydrogen peroxide, pertrifluoroacetic acid, sodium periodate, sodium hypochlorite, potassium permanganate, Dess-Martin periodate, dimethyl Sulfoxide / oxalyl chloride (Swern oxidation), ruthenium catalyst, etc. can be used, and the reaction may be carried out at -80 ° C to 50 ° C.
  • Solvents include tetrahydrofuran, dimethylformamide, jetyl ether, dichloromethane, toluene, benzene, xylene, cyclohexane, hexane, chloroform, ethyl acetate, butyl acetate, pentane, heptane, dioxane, acetone, acetonitrile, water. , Methanol, ethanol, isopropanol, and mixed solvents thereof can be used.
  • Compound (IA) can be obtained by subjecting the obtained compound 10 and an amino compound 7 having substituents Z and R 7 corresponding to the target compound to a reductive amination reaction by a conventional method.
  • Reducing agents include sodium borohydride, sodium triacetoxyborohydride, and cyano hydride.
  • Sodium silicon or the like can be used, and the reaction may be performed at 0 ° C to 50 ° C.
  • As the solvent tetrahydrofuran, dimethylformamide, dioxane, acetonitrile, methanol, ethanol, propanol, acetic acid, hydrochloric acid, and a mixed solvent thereof can be used.
  • Compound 12 can be obtained by reacting compound 1 with acyl halide 11 having substituent R 1 corresponding to the target compound in an appropriate solvent at 20 ° C. to 50 ° C. for several minutes to several hours.
  • Solvents include tetrahydrofuran, dimethylformamide, jetyl ether, dichloromethane, toluene, benzene, xylene, cyclohexane, hexane, chloroform, ethyl acetate, butyl acetate, pentane, heptane, dioxane, acetone, and acetonitrile. Water, a mixed solvent thereof or the like can be used.
  • Compound (I-B) according to the present invention can be obtained by subjecting Compound 12 thus obtained to the methods similar to Step D, Step G, Step H and the above-mentioned method.
  • R is alkyl
  • substituent R 7 is introduced into compound 16.
  • ⁇ ⁇ ⁇ 1 is by reacting in the presence of salt based on halogen) to give compound 17.
  • Tetrahydrofuran and dimethylformamide can be used as the solvent. The reaction can be performed at room temperature.
  • the base triethylamine, pyridine, dimethylaminopyridine and the like can be used.
  • IC a compound in which R 7 is hydrogen does not perform this step.
  • substituent 17 is introduced into compound 17.
  • ⁇ ⁇ ⁇ 1 is by reacting a halogen) under basic existence, to give compound 18.
  • a halogen a halogen
  • methanol, ethanol, isopropanol, dimethylformamide or the like can be used as the solvent. The reaction is
  • it can be carried out using a sealed tube and a microwave reactor.
  • As the base ⁇ , ⁇ -diisopropylethylamine, etc. are used. It is possible to be.
  • compound 18 is reduced to obtain compound 19.
  • a reducing agent lithium aluminum hydride can be used. Tetrahydrofuran or the like can be used as the solvent. The reaction can be carried out at room temperature.
  • compound 19 is azidated to give compound 20.
  • compound 19 is reacted with methanesulfuryl chloride using triethylamine as a base to induce compound 19 to mesylate.
  • the solvent for the mesyl chloride black mouth form can be used.
  • the obtained compound can be reacted with sodium azide and subjected to azidoxy in dimethylformamide or the like at room temperature or under heating to obtain compound 20.
  • compound 20 is reduced to obtain compound 21. It can be carried out by catalytic reduction.
  • the catalyst 10% palladium carbon or the like can be used.
  • the solvent ethanol or the like can be used.
  • R 1 — Y— X ⁇ X 1 is halogen, etc., Y is S, SO, SO or CO
  • compound 22 is reacted to obtain compound 22.
  • R 1 —Y—X 1 various sulfo-ork mouth-rides, and silk silk mouth-rides can be used.
  • the solvent tetrahydrofuran, dimethylamide, or the like can be used.
  • the reaction can be carried out at room temperature or under heating. Pyridine, triethylamine and the like can be used as a base that is preferably carried out in the presence of a base.
  • the compound in which R 2 is hydrogen does not perform the subsequent step R, and the compound 22 is the final target compound.
  • ⁇ SO
  • substituent R 2 is introduced into compound 22.
  • ⁇ ⁇ ⁇ 1 is halogen
  • Compound (I—C) can be obtained by reacting with compound 22 in the presence.
  • the base sodium hydride or the like can be used.
  • the solvent dimethylformamide and the like can be used.
  • R is optionally substituted lower alkyl
  • R 7 is hydrogen or optionally substituted lower alkyl
  • G is 1,4-cycloalkylene
  • Z may have a substituent! / May be! /
  • a hydrocarbon cyclic group or a substituent may be a heterocyclic group
  • R is particularly preferably lower alkyl, more preferably methyl or ethyl. Ethyl is particularly preferable.
  • R 7 is preferably hydrogen.
  • Z may have a substituent! /, But a heterocyclic group is preferred.
  • z is pyridyl which may have a substituent, pyridazil which may have a substituent, Pyradul which may have a substituent, Pyrimidinyl which may have a substituent, Quinolyl which may have a substituent, Isoquinolyl which may have a substituent, Benzothiazolyl, which may have a substituent, Benzoxazolyl which may have a substituent, Benzopyridyl which may have a substituent, Benzopyridyl which may have a substituent, Benzimidazolyl, with a substituent!
  • R is alkyl, Pro is an amino protecting group
  • a protecting group is introduced into compound 17.
  • the protecting group the protecting groups described in Protective Groups in Organic Synthesis (by Theodra W. Greene) can be used.
  • Amino protecting groups that can be removed under acidic conditions are preferred. Examples thereof include a benzyloxycarbonyl group and a tert-butyloxycarbonyl group.
  • ProX ⁇ X 1 is halogen
  • Pro is benzyloxycarbon group, tert-butyloxycarbol, etc.
  • Pro-O-Pro Pro is benzyloxycarbol group, tert Compound 23 can be obtained by reacting in the presence of a base. Tetrahydrofuran and dimethylformamide can be used as the solvent.
  • the reaction can be performed at room temperature.
  • the base triethylamine, pyridine, dimethylaminopyridine and the like can be used. It is to be noted that the reaction can be similarly carried out even when R 7 is a hydrogen compound.
  • compound 23 is reduced to obtain compound 24.
  • a reducing agent lithium aluminum hydride can be used. Tetrahydrofuran or the like can be used as the solvent. The reaction can be carried out at room temperature.
  • compound 24 is azidated to give compound 25.
  • compound 24 is reacted with methanesulfuryl chloride using triethylamine as a base to induce compound 24 to mesylate.
  • the solvent for the mesyl chloride black mouth form can be used.
  • the resulting compound is reacted with sodium azide, and subjected to azidolysis in dimethylformamide or the like at room temperature or under heating to obtain compound 25.
  • compound 25 is reduced to obtain compound 26.
  • Reduction of compound 25 with triphenylphosphine and water provides compound 26.
  • the reaction can be performed under warming. Tetrahydrofuran can be used as the solvent.
  • it can be carried out by catalytic reduction. In the case of catalytic reduction, 10% palladium carbon or the like can be used as a catalyst.
  • As the solvent ethanol or the like can be used. Which reduction method is used depends on the protecting group used. You can choose.
  • R 1 — Y— X ⁇ X 1 is halogen, etc., Y is S, SO, SO or CO
  • compound 27 is reacted to give compound 27.
  • R 1 —Y— 1 is a halogen or the like, various sulfonyl chlorides, alkyl silks and the like can be used.
  • the solvent tetrahydrofuran, dimethylamide, or the like can be used.
  • the reaction can be carried out at room temperature or under warming. Pyridine, triethylamine, etc. can be used as a base that is preferably carried out in the presence of a base.
  • the protecting group of compound 27 is removed.
  • Various conditions can be selected and used depending on the protecting group for removing the protecting group.
  • the tert-butyloxycarbol group can be removed with an acid.
  • the benzyloxycarbonyl group can be removed by catalytic reduction or the like.
  • substituent Z is introduced into compound 28.
  • compound (ID) can be obtained by reacting ZX ⁇ X 1 with halogen in the presence of a base.
  • a base methanol, ethanol, isopropanol, dimethylformamide and the like can be used.
  • the reaction can be carried out at room temperature or under warming. For example, it can be carried out by sealing the tube and using a microwave reactor.
  • ⁇ , ⁇ -diisopropylethylamine and the like can be used as the base.
  • R is optionally substituted lower alkyl
  • Pro is a protecting group
  • R 7 has hydrogen or a substituent, and may be lower alkyl
  • G is 1,4-cycloalkylene
  • Y is SO or SO
  • R 1 is an optionally substituted lower alkyl
  • R 2 has hydrogen or a substituent, and may be lower alkyl
  • R is particularly preferably lower alkyl, more preferably methyl or ethyl. Ethyl is particularly preferable.
  • Pro is preferably an amino protecting group that can be removed under acidic conditions.
  • R is optionally substituted lower alkyl, optionally substituted lower alkyl.
  • tert-butyloxycarbonyl group is preferred! /.
  • R 7 is preferably hydrogen.
  • Y is preferably SO.
  • R 1 is particularly preferably lower alkyl, more preferably isopropyl or ethyl. Ethyl is particularly preferable.
  • R 2 is preferably hydrogen.
  • R is ethyl or tert-butyl.
  • R 1 is ethyl, isopropyl or tert-butyl.
  • Z is a hydrocarbon cyclic group which may have a substituent or a heterocyclic group which may have a substituent).
  • R 1 may have a substituent and may be lower alkyl (hereinafter, R 1 is R1-1).
  • R 1 is alkyl of each Nono androgenic carbon atoms, which may be substituted with 1-10 (hereinafter, R 1 is assumed to be R1- 2) compounds,
  • R 1 is an alkyl having 1 to 10 carbon atoms which may be substituted with halogen (hereinafter, R 1 is assumed to be R 1 3) compound,
  • R 1 is isopropyl or t-butyl
  • R 2 is hydrogen or an alkyl having 1 to 3 carbon atoms
  • R 2 force is 3 ⁇ 42-1) Compound
  • R 2 is R 2 -2
  • X may have a substituent, may be lower alkylene, may have a substituent, and may be lower alkyl.
  • May have a substituent may have a cycloalkylene, have a substituent! /, May have a cycloalkylene, may have a substituent, a bicycloalkylene, have a substituent
  • X is alkylene having 2 to 6 carbon atoms, alkylene having 3 to 6 carbon atoms, or
  • May have a substituent may have a cycloalkylene, have a substituent! /, May have a cycloalkylene, may have a substituent, a bicycloalkylene, have a substituent
  • the optionally substituted phenylene, the optionally substituted piveridylene, the optionally substituted thiopheneyl or the optionally substituted flangeyl (hereinafter, X is X—2) compound,
  • X is alkylene having 2 to 6 carbon atoms or
  • May have a substituent may have a cycloalkylene, have a substituent! /, May have a phenol, may have a substituent, may have a substituent, may have a substituent.
  • a thiophene diyl which may optionally be substituted or a furilyl which may have a substituent hereinafter, X is assumed to be X-3
  • X is alkylene having 2 to 6 carbon atoms, or substituted with each of halogeno, hydroxy, lower alkyl or halogeno lower alkyl, and is cycloalkylene or phenylene (hereinafter, X is X-4).
  • X is alkylene having 3 to 6 carbon atoms or 1,4-cyclohexylene (hereinafter, X is X-6),
  • Z may have a substituent, may be lower alkyl, may have a substituent! /, May be a hydrocarbon cyclic group or an optionally substituted heterocyclic group.
  • a compound hereinafter Z is Z-1),
  • Z is one (CR 8 R 9 ) r— W— (CR 10 R) sV
  • R 8 , R 9 , R 1C) and R 11 are each independently hydrogen or lower alkyl, and when two or more R 8 , R 9 , R 10 and / or R 11 are present, Each R 8 , R 9 , R 10 and R 11 may be different W is a single bond, 0, S or NR 12 , R 12 is hydrogen, lower alkyl or phenol, V Is hydrogen, optionally substituted cycloalkyl, substituted May be a bicycloalkyl, may have a substituent! /, May be aryl or a heterocyclic group which may have a substituent, and r is 1 to Is an integer of 4 and s is an integer from 0 to 4]
  • Z is Z-2
  • W is a single bond, 0, S or NR 12 , R 12 is hydrogen or lower alkyl
  • V may have a substituent, respectively, an aryl or heterocyclic group
  • the substituent is halogen, hydroxy, lower alkyl, halogeno lower alkyl, lower alkoxy, lower alkyl, amide-containing lower alkyl amide-acyl, carboxy, lower alkoxycarbole, phenol or monocyclic helium.
  • r is an integer from 1 to 4
  • s is an integer from 0 to 4]
  • Z is Z-3
  • W is a single bond, 0, S, NH or NMe
  • V may have a substituent, respectively, a phenyl or a heteroaryl (wherein the substituents are halogen, lower alkyl, Halogeno lower alkyl, lower alkoxy, amino or lower alkylamino), r is an integer of 1 to 3, and s is 0 or 1]
  • Z is Z-4
  • Z may have a substituent, and may be a hydrocarbon cyclic group.
  • Lower alkyl which may have a substituent (wherein the substituent is halogen, hydroxy, carboxy, lower alkoxycarbo, cyan and Z or phenol);
  • Substituted with a lower alkoxy carbocycle may be a lower alkell
  • Lower alkoxy which may have a substituent (wherein the substituent is halogen, hydroxy, lower alkoxy, carboxy, lower alkoxycarbole, lower alkylamido cycloalkyl, cyano and Z or heterocyclic group) ;
  • Phenyloyl optionally substituted by halogen, sheared phenyl and / or heterocyclic groups
  • It may have a substituent, and may be a heterocyclic group (wherein the substituent may be protected, hydroxy; mercapto; halogen; lower alkyl; cycloalkyl; lower alkoxycarbol; acyl) Low alkoxycarbonyl; oxo; phenol; lower alkoxy phenol; halogenophenol; heterocyclic group and z or oxo); substituted with lower alkyl! Heterocyclic sulfol; heterocyclic oxy; substituted with lower alkyl !, may! /, Heterocyclic carbo]
  • Z is Z-5
  • Z has a substituent! /, May! /
  • the substituent is halogen; hydroxy; nonogen, hydroxy, lower alkoxy carbo, cyan and / or phenyl, which may be substituted, lower alkyl; lower alkoxy carboxy lower alkenyl.
  • Lower alkyl sulfamoyl; cycloalkyl sulfamoyl; -tro; alkylene dioxy; may be substituted with lower alkyl ⁇ erazo; phenoxy; oxo; Si, halogen, lower alkyl, lower alkoxy carboyle, amylin rubamoyl, fue
  • V ⁇ heterocyclic sulfol (hereinafter, Z is Z-6),
  • Z has a substituent! /, May! /
  • substituents are halogens; nonogens, hydroxys, lower alkoxycarbols and
  • Lower alkyl optionally substituted with Z or phenyl; optionally substituted with norogen and Z or cycloalkyl; lower alkoxy; cycloalkyl; cycloalkyl; cycloalkyl; lower alkylthio; Substituted with lower alkyl, hydroxy lower alkyl, acyl and / or phenyl, optionally amino; substituted with piperidyl, phenyl; cycloalkylsulfamoyl; alkylene diene Xy; phenoxy;
  • Substituted with lower alkyl may be morpholinyl or morpholino; substituted with hydroxy, lower alkyl, lower alkoxy carbole, phenol, halogenophenol and z or oxo, piperidyl; hydroxy , Substituted with rubamoyl and / or oxo, pyrrolidyl; substituted with phenol or pyrimidyl; and piperazil; dihydropyridyl; pyrrolyl; pyrrolinyl; halogen and z or Substituted with lower alkyl, may be imidazolyl; pyrazolyl; chael; thiadiazolyl; furyl; oxazolyl; isoxazolyl; may be substituted with lower alkyl and Z or fur, may be tetrazolyl; Indolyl; tetrahydroquinolyl; substituted with lower alkyl, Benzothiazolyl; substituted with
  • Z Tetrahydroisothiazolyl; substituted with oxo, benzovir; tetrahydroviraroxy; tetrahydrofuryloxy; lower alkyl And / or morpholinosulfol; and / or pylidylsulfol substituted with lower alkyl (hereinafter Z is Z-7) ,
  • Z has a substituent! /, May! /, Phenol (wherein the substituents are halogen, lower alkyl, halogeno lower alkyl, lower alkoxy, cycloalkyloxy, lower alkylcarbamoyl, phenol) , Lower alkylmorpholino and Z or tetrahydrovillaroxy (Hereinafter, Z is Z-8),
  • Z may be substituted with a heterocyclic group (wherein the substituents are halogen, hydroxy, lower alkyl, halogeno lower alkyl, lower alkoxy, mercapto, lower alkylthio, acyl, carboxy, lower alkoxy) Carbo, amide-containing lower alkyl amide-containing phenyl, naphthyl, optionally substituted with phenylthio, optionally substituted with halogen, optionally substituted with phenoxy, oxo and / or lower alkyl V, a heterocyclic group) (hereinafter, Z is Z-9),
  • Z may optionally have a substituent, such as phenyl, pyrazolyl, thiazolyl, thiadiazolyl, pyridyl, pyrimidyl, pyrajyl, pyridazyl, ⁇ riazyl, indolyl, isoindolyl, indolyl, isoindoleyl.
  • a substituent such as phenyl, pyrazolyl, thiazolyl, thiadiazolyl, pyridyl, pyrimidyl, pyrajyl, pyridazyl, ⁇ riazyl, indolyl, isoindolyl, indolyl, isoindoleyl.
  • Each Z may have a substituent such as phenyl, thiazolyl, thiadiazolyl, pyridyl, pyrajur, indolyl, isoindolinyl, benzopyranyl, quinolyl, carbazolyl, dibenzofuryl, benzovir, benzocher or benzothiazolyl Substituent is lower alkyl, halogeno lower alkyl, lower alkoxy, lower alkoxy force group, asyl, phenol, naphthyl, phenol, lower alkyl morpholino and oxo force group force selected 1 or more Group) (hereinafter Z is Z-11)
  • R 1 is R1-2, R 2 is R2-2, n is 2, and a combination of X, Y and Z (X, Y, Z) is
  • (X, Y, Z) (X- 3, Y-2, Z-1), (X-3, Y- 2, Z- 2), (X- 3, Y- 2, Z- 3), (X- 3, Y— 2, Z -4), (X-3, Y-2, Z-5), (X-3, Y-2, Z-6), (X- 3, Y-2, ⁇ -7), (X-3 , ⁇ -2, ⁇ -8), (X-3, ⁇ -2, ⁇ -9), (X-3, ⁇ -2, ⁇ -10), (X-3, ⁇ -2, ⁇ -11) ),
  • the ⁇ 5 receptor antagonist of the present invention acts effectively on all diseases related to ⁇ 5, but is particularly useful for the prevention and treatment of obesity or suppression of eating. It is also effective for prevention and / or treatment of diseases in which obesity is a risk factor, such as diabetes, hypertension, hyperlipidemia, arteriosclerosis, and acute coronary syndrome.
  • the compound of the present invention has not only a 5 receptor antagonism but also a usefulness as a medicament, and has any or all of the following excellent features.
  • the NPY Y5 receptor antagonist of the present invention has a high affinity for NPY Y1 and Y2 receptors with low affinity for Y5 receptor.
  • NPY induces persistent defect contraction in the periphery, but this action is mainly mediated by the Y1 receptor. Since the Y5 receptor is not involved in such an action at all, it is considered that the Y5 receptor can be suitably used as a safe pharmaceutical with a low possibility of inducing side effects based on peripheral vasoconstriction.
  • the NPY Y5 receptor antagonist suppresses food intake and exhibits an anti-obesity effect. For this reason, it is central to the side effects such as indigestion that are seen in drugs that exhibit anti-obesity effects by inhibiting digestion and absorption, and the antidepressant action such as serotonin transporter inhibitors that exhibit anti-obesity effects.
  • side effects such as indigestion that are seen in drugs that exhibit anti-obesity effects by inhibiting digestion and absorption
  • the antidepressant action such as serotonin transporter inhibitors that exhibit anti-obesity effects.
  • One of the features of this drug is that it does not cause side effects.
  • the compound according to the present invention when administered as an anti-obesity agent or an antifeedant, it can be administered either orally or parenterally.
  • Oral administration may be prepared and administered in a commonly used dosage form such as tablets, granules, powders, capsules, pills, solutions, syrups, knockers or sublinguals according to conventional methods.
  • any commonly used dosage forms such as injections such as intramuscular administration and intravenous administration, suppositories, transdermal absorption agents, and inhalants can be suitably administered. Since the compound according to the present invention has high oral absorbability, it can be suitably used as an oral preparation.
  • lactose sucrose, glucose, starch, calcium carbonate, or crystalline cellulose is used as an excipient, and methylcellulose, carboxymethylcellulose, hydroxypropylcellulose, gelatin, or polybulurpyrrolidone is used as a binder.
  • disintegrants carboxymethylcellulose, sodium carboxymethylcellulose, starch
  • examples of the lubricant include talc, magnesium stearate, and macrogol.
  • a solubilizing agent, suspending agent, emulsifying agent, stabilizing agent, preservative, isotonic agent, etc. that are usually used are added as appropriate.
  • a flavoring agent, fragrance or the like may be added.
  • the dose of the compound according to the present invention as an anti-obesity agent or an anti-feeding agent is preferably set in consideration of the patient's age, weight, type and degree of disease, administration route, etc. When administered orally to adults, it is usually 0.05-: LOOmgZkgZ days, preferably 0.
  • the force varies greatly depending on the administration route. Usually, it is 0.005 to 10 mgZkgZ ⁇ , preferably within the range of 0.01 to LmgZkgZ ⁇ . This may be administered once to several times a day.
  • 3-Fluoro-trobenzene (2.00 g, 14.2 mmol) is dissolved in 15 ml of dimethyl sulfoxide, and 3,5-dimethylbiperidine (3.21 g, 28.4 mmol) and potassium carbonate (3.92 g, 28.4 mmol) are added. Stir for 3 hours at 150 ° C. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate.
  • the compound obtained in the third step (500 mg, 2.01 mmol) was dissolved in 5 ml of black mouth form, des-tin periodate (893 mg, 2.11 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The precipitate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to obtain the desired aldehyde (385 mg, yield 77%).
  • the raw material amine (1.20 g, 3.64 mmol) and 2-chloro-5-trifluoromethylpyridine (727 mg, 4.0 1 mmol) were suspended in 4 ml of isopropanol, and N, N-diisopropylethylamine (1.87 m 1, 10.9 mmol) was sealed, and the reaction was carried out at 160 ° C for 1 hour using a microwave reactor.
  • the reaction mixture was poured into water and extracted with ethyl acetate.
  • the organic layer is washed with water and anhydrous Dried over sodium sulfate.
  • the solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography to obtain 222 mg of the desired ester in a yield of 20%.
  • Methanesulfurol mouthride (0.12 ml, 1.64 mmol) was added dropwise under ice cooling and stirred at room temperature for 1 hour. .
  • the reaction solution was poured into water and extracted with ethyl acetate, the organic layer was washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain mesylate.
  • the obtained mesylate was dissolved in 3 ml of dimethylformamide, sodium azide (221 mg, 3.40 mmol) was added, and the mixture was stirred at 100 ° C for 3 hours.
  • the reaction mixture was poured into water and extracted with ethyl acetate.
  • the organic layer was washed with water and dried over anhydrous sodium sulfate.
  • the solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography to obtain 178 mg of the target product, a yield of 87%.
  • Lithium aluminum hydride (18.3 g, 483 mmol) was suspended in 800 ml of tetrahydrofuran, and the tetrahydrofuran solution (300 ml) of the ester obtained in the first step was slowly added over 1 hour with stirring under ice cooling. . After reacting for 10 minutes under ice cooling, the reaction was further allowed to proceed at room temperature for 2.5 hours. The reaction mixture was ice-cooled again, a mixture of water and tetrahydrofuran (1: 1, 36 ml), 2N aqueous sodium hydroxide solution (18 ml) and water (18 ml) were added in this order, and the mixture was stirred for 20 min.
  • the azide obtained in the third step was dissolved in 900 ml of tetrahydrofuran at room temperature, triphenylphosphine (103 g, 392 mmol) and water (90 ml) were sequentially added, and the mixture was reacted at 80 ° C. for 1.5 hours.
  • 770 ml of the solvent was distilled off, and 300 ml of water, 400 ml of ethyl acetate, and 150 ml of 2N hydrochloric acid were added in this order to adjust the pH to 2.5, followed by liquid separation extraction.
  • the organic layer was extracted with 2N hydrochloric acid, and the aqueous layers were combined and washed with ethyl acetate.
  • the starting amine (37.5 g, 164 mmol) was suspended in 400 ml of tetrahydrofuran, (91.7 ml, 656 mmol) and isopropyl sulfochloride (32.2 ml, 416 mmol) were added slowly in this order while stirring at -55 to -40 ° C, and the reaction was continued for 6 hours while gradually warming to 0 ° C. I let you.
  • the reaction mixture was poured into an ice-cooled dilute aqueous acid solution and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and isopropyl ether was added to the residue. The precipitated crystals were collected by filtration and washed with isopropyl ether to obtain 43.1 g of the desired sulfonamide in a yield of 79%. .
  • Boc protected raw amine 43.0 g, 128 mmol
  • 4N hydrochloric acid-dioxane solution (96 ml, 384 mmol) was stirred with ice-cooling and allowed to react for 20 minutes. And further reacted at room temperature for 3 hours.
  • the reaction mixture was ice-cooled again, and 20 ml of isopropyl ether was added and stirred for 30 minutes.
  • the precipitated crystals were collected by filtration and washed with isopropyl ether to obtain 30.8 g of the target ammine hydrochloride. Yield 89%.
  • R 1 is an ethyl group
  • R 1 is a tert-butyl group
  • J is 1 to 0
  • ⁇ ⁇ ⁇ 8 f ⁇ 2 ' ⁇ ) ⁇ 9 ⁇ 9'

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US12/226,516 US9150507B2 (en) 2006-04-28 2007-04-25 Amine derivative having NPY Y5 receptor antagonistic activity
MX2008013511A MX2008013511A (es) 2006-04-28 2007-04-25 Derivados de amina que tienen actividad antagonista del receptor neuropeptido y y5.
AU2007244358A AU2007244358B2 (en) 2006-04-28 2007-04-25 Amine derivative having NPY Y5 receptor antagonist activity
EP07742373.9A EP2017261A4 (en) 2006-04-28 2007-04-25 AMINE DERIVATIVE HAVING ANTAGONIST ACTIVITY OF NPY Y5 RECEPTOR
CA002650683A CA2650683A1 (en) 2006-04-28 2007-04-25 Amine derivative having npy y5 receptor antagonist activity
CN200780024349.7A CN101479238B (zh) 2006-04-28 2007-04-25 具有npyy5受体拮抗活性的胺衍生物
NZ572381A NZ572381A (en) 2006-04-28 2007-04-25 Amine derivative having npy y5 receptor antagonist activity
JP2008513237A JP4528901B2 (ja) 2006-04-28 2007-04-25 Ｎｐｙｙ５受容体拮抗作用を有するアミン誘導体
BRPI0710950-4A BRPI0710950A2 (pt) 2006-04-28 2007-04-25 derivado de amina tendo atividade antagonìstica de receptor y5 de npi 53 a61p 3/04 a61p 9/04 a61p 9/12 a61p 15/00 a61p 25/08 a61p 25/20 a61p 25/24 a61p 43/00 c07c 311/07 c07c 317/36 c07d 207/325 c07d 211/14 c07d 213/38 c07d 213/74 c07d 213/82 c07d 215/38 c07d 217/04 c07d 217/14 c07d 217/22 c07d 219/10 c07d 231/38 c07d 233/61 c07d 235/30 c07d 237/20 c07d 237/22 c07d 237/34 c07d 239/42 c07d 241/20 c07d 261/14 c07d 261/20 c07d 263/58 c07d 265/30 c07d 265/36 c07d 267/14 c07d 275/02 c07d 277/28 c07d 277/62 c07d 277/82 c07d 295/12 c07d 295/18 c07d 333/36 c07d 333/40 c07d 333/66 c07d 333/72 c07d 403/04 c07d 409/04 c07d 413/04 c07d 417/12 c07d 498/04 c07d 513/04
KR1020087026246A KR101441146B1 (ko) 2006-04-28 2007-04-25 Ｎｐｙ ｙ5 수용체 길항 작용을 갖는 아민 유도체
NO20084983A NO20084983L (no) 2006-04-28 2008-11-27 Aminderivat med NPY Y5 reseptorantagonistaktivitet
US12/823,568 US9139518B2 (en) 2006-04-28 2010-06-25 Amine derivative having NPY Y5 receptor antagonistic activity

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WO2011065351A1 (ja) 2009-11-25 2011-06-03 塩野義製薬株式会社 シクロヘキサン誘導体の製造方法
JP2013525376A (ja) * 2010-04-23 2013-06-20 サイトキネティクス・インコーポレーテッド 特定のアミノピリダジン、その組成物、及びこれらの使用方法
WO2011157827A1 (de) 2010-06-18 2011-12-22 Sanofi Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen
WO2012120055A1 (de) 2011-03-08 2012-09-13 Sanofi Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung
WO2012120056A1 (de) 2011-03-08 2012-09-13 Sanofi Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung
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MX2008013511A (es) 2008-10-28
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AU2007244358A1 (en) 2007-11-08
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JP4528901B2 (ja) 2010-08-25
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